8 Amazing Ways to Wear Shirtdress with High Boots

By Kaia Saunders / Updated on November 15, 2018
Pretty street style examples of woman wearing shirtdress with high boots. Find out how to wear these versatile and comfy extended shirts in a most alluring way. #shirtdresses

The shirtdress is one of the most classic items that one woman can have in her wardrobe. It is versatile, comfy and most of all you will feel very comfortable while wearing it.

Whether you decide to pair it with sneakers, high boots or kitten heels, one is sure – you can absolutely wear it for any occasion, working place or drink with your colleagues in the evenings. In this article, we will focus on how to combine shirt dress and high boots properly.

Shirtdress Accessory Essentials

The shirtdress pattern and fabric may be great, but actually, it is the shoes that set the tone for the outfit. But there are other items as well that can make you look stylish. Does your body size matter when you consider wearing short shirtdress? NO! It does matter as long as you blend well your outfit.

The accessory you can always call for help is a belt. Thin or with decorated buckle – whether you choose will make you unique.

However, wearing it without a belt or any other accessory can show your effortless side – you will look sophisticated, but it will be evident that it is in your nature.

You can always incorporate hats, leggings or tights to your outfit to make it more fun yet appropriate. However, leggings or tights can only be worn when you are wearing a short shirtdress and ankle-high boots, so that you do not appear overdressed.

The biggest issue is to choose which boots will make a good combo with your shirtdress. Shirtdresses are classy yet flirty so no matter what you do – do not take away these qualities from your outfit.

When you decide to wear a long shirtdress, then ankle-high boots will be the most appropriate. However, this exception is just for a delicately designed shirtdress that may have a longer slit; then you can wear knee-high boots. Follow these rules to avoid the fashion faux-pas.

The length of your hemline will determine how high your boots go. However, depending on how generous you feel showing off your legs you can try it with ankle-high boots.

We will try to find some ideas on how to blend well your shirtdress and high boots to make heads turn as you walk down the streets. We love attractive outfits so any decent outfit that can make you look classy, and be head-turners – we are definitely down for it.

Wearing Shirtdress with Thigh-High Boots

There are some days when you want to dress to impress. When you choose to wear shirtdress and thigh-high boots you have to know the do’s and don’ts. Let’s see how you can look fabulous, yet very classy when mixing super trendy thigh-high boots and shirtdress.

Denim Shirtdress with Suede Thigh-High Boots

Even though this shirtdress is short and bit revealing, this girl soothes it down with super thigh-high boots. What a sexy look!Photo: pinterest.com

Even though this shirtdress is short and bit revealing, this girl soothes it down with super thigh-high boots. They play a double role here – as boots and tights as well!

The material of the boots is suede, which is perfect for everyday wear. When it comes to other accessories, this fashionista opted for a wide belt in black color. She highlights her waist and adds a nice touch to this comfy yet sexy outfit combination.

White Shirtdress with Cowboy Thigh-High Boots

Wake up your inner cowgirl with these fantastic snakeskin boots! They look absolutely amazing in combination with a classy white shirtdress.Photo: pinterest.com

Wake up your inner cowgirl with these fantastic snakeskin boots!

They look absolutely amazing in combination with a classy white shirtdress. A thin belt around your waist is a perfect detail that catches attention as well as boots. If you like to layer your clothes down, then style a turtleneck under the shirtdress. It will give you a bold look.

Plaid Shirtdress with Thigh-High Boots

Youngish and stylish - two words that can describe this lovely outfit. Black thigh-high boots are styled with super short (and sweet) plaid shirtdress.Photo: pinterest.com

Youngish and stylish – two words that can describe this lovely outfit.

Black thigh-high boots are styled with super short (and sweet) plaid shirtdress. However, with the long trench coat layered down the dress, you can avoid the inappropriate look.

Dressed like this, you can go to a concert, dinner with friends and any other stylish event.

3 Ways to Wear Shirtdress with Knee-High Boots

Similar to the thigh-high boots, these are perfectly comfortable, and they work amazingly good with a shirtdress.

There was always something exciting and intriguing in showing off a bit of skin. Try to wear a shirtdress that has a hemline right above the boots.

White Shirtdress with Patterned Knee-High Boots

Such patterned boots are the head turner. Even though they are styled with simple and chic white shirtdress, they still look amazing.Photo: pinterest.com

Did you ever think about wearing patterned boots? If you are nodding negatively, then we have something that will change your mind.

These high boots are the head turner. Even though they are styled with simple and chic white shirtdress, they still look amazing.

Striped Shirtdress with Brown Knee-High Boots

It is known that stripes and brown leather boots make a perfect combination. This outfit is great for a girl’s night out, as well as for casual city stroll.Photo: pinterest.com

It is known that stripes and brown leather boots make a perfect combination.

This outfit is great for a girl’s night out, as well as for casual city stroll. You can be sure about one thing – feeling comfy is inevitable!

Blue Midi Dress with Suede Knee-High Boots

Patterned shirtdress will be one of your most favorite items in your wardrobe. Why? Because it is perfectly versatile and flattering to your body line.Photo: louellareese.com

Patterned shirtdress will be one of your most favorite items in your wardrobe. Why? Because it is perfectly versatile and flattering to your body line.

Wearing it with knee-high suede boots is the right choice.

Combining Shirtdress with Ankle-High Boots

Ankle boots might be one of the most favorite footwear of all stylish girls around the world. They are versatile, so chic and comfy.

In combination with a shirtdress, the ankle-high boots can transform even the most casual outfits into the interesting ones.

Asymmetric Shirtdress with Ankle-High Boots

White and olive green in one outfit makes a perfect combo! This shirtdress has an asymmetric cut, which makes it even more interesting. The blazer represents a classy piece that you need to have in your closet.Photo: pinterest.com

White and olive green in one outfit makes a perfect combo!

This shirtdress has an asymmetric cut, which makes it even more interesting. The blazer represents a classy piece that you need to have in your closet.

Don’t be afraid of colors!

Sleeveless Shirtdress with Ankle-High Boots

Black and white combos are just timeless. No matter how much you like other shades - these are outfits that you always go back to.Photo: pinterest.com

Black and white combos are just timeless. No matter how much you like other shades – these are outfits that you always go back to.

This model-off-duty look is perfect for everyday wear. Comfortable and very stylish – fantastic mix!

Chunky Shirtdress with Ankle-High Boots

Peep-toe booties are trendy and bit challenging for wearing. However, you can be completely sure with a shirtdress.Photo: pinterest.com

Peep-toe booties are trendy and bit challenging for wearing. However, you can be completely sure with a shirtdress. It is a fashion-approved combination that you can wear for working hours as well as for casual occasions.

Add some bold detail – colorful bag or big sunglasses.

Casual and Funky Looks with Shirt Dresses

This is the time you show your creativity in fashion.

You can never go wrong with dark denim on a casual Friday. You don’t want to be overdressed still you have to pull your A-game even when it is just a pizza time-out or drinks with your friends. The shirtdress is usually comfy so you can do all these activities without second-guessing your outfit.

Try not to look like a clown, but if you are daring, you can mix prints which will bring out your personality. For casual days we prefer to recommend minimalistic accessories because it’s a fun day with friends and you might plan for a pizza date and then impromptu swimming. Friends are unpredictable when together.

You can still rock a casual and funky look with a shirtdress and high boots even on chillier days.It is essential to know how to blend the outfit so that you remain warm and cozy. Tights or leggings usually go a long way in complementing shirtdress in cold weather. They keep you warm yet do not steal the show from the shirtdress making your outfit rock the way you want it to.

Black Denim Shirtdress with Suede Thigh-High Boots

This look is classy, chic and very casual. Most of all, you will feel comfortable, while remain looking pretty great!Photo: pinterest.com

This look can be perfect for all these things mentioned before – pizza night out, movie night, or just a drink with your besties. It is classy, chic and very casual.

Most of all, you will feel comfortable, while remain looking pretty great!

Short Shirtdress with Red Thigh-High Boots

Colorful shoes might be something that you were not planning to wear, but can we take a moment and look at these lovely red thigh-high boots? They are matched perfectly with a white shirtdress and the olive-green denim jacket above.Photo: pinterest.com

Colorful shoes might be something that you were not planning to wear, but can we take a moment and look at these lovely red thigh-high boots?

They are matched perfectly with a white shirtdress and the olive-green denim jacket above.

Maxi Baby Blue Shirtdress with Ankle-High Boots

Brocat ankle boots were at the peak of their popularity last fall and during the wintertime. However, you can be a bit creative and mix them with lovely and very comfortable maxi baby blue shirtdress.Photo: pinterest.com

Brocat ankle boots were at the peak of their popularity last fall and during the wintertime.

However, you can be a bit creative and mix them with lovely and very comfortable maxi baby blue shirtdress.

How to Wear Shirtdress in Winter

If you have thought that wearing shirtdresses is reserved only for warm weather conditions, you were quite wrong.

With tights and warm high boots, you can wear your favorite shirtdresses anytime you wish. Try to layer it with a chic trench coat, military parka jacket or long elegant coat.

Emerald Green Shirtdress with Black Thigh-High Boots

Combination of materials and colors of this outfit is just fantastic. Camel coat can work perfectly with emerald green silk shirtdress.Photo: pinterest.com

Combination of materials and colors of this outfit is just fantastic. As you can see, camel coat can work perfectly with emerald green silk shirtdress. You can always make it more interesting by adding some colorful detail.

This red bag is exactly what we were thinking about!

Cozy Shirtdress with Grey Suede Thigh-High Boots

Keeping yourself cozy should always come before trying to look stylish. Grey tones make outfits warmish so you can combine white and grey shades if you want to wear it in the wintertime.Photo: pinterest.com

Keeping yourself cozy should always come before trying to look stylish. Grey tones make outfits warmish so you can combine white and grey shades if you want to wear it in the wintertime.

Oversized Shirtdress with Purple Thigh-High Boots

Emerald silhouette-friendly dress is perfect for wearing on the cold fall days.Photo: wendyslookbook.com

We love oversized and comfy items. The best are the ones that are chic and easy to style. This emerald silhouette-friendly dress is perfect for wearing on the cold fall days.

3 Outfit Examples With Oversized T-shirts and High Boots

We can advise you to wear a shirtdress that is soft and comfy, but you have to look a little bit further than normal.

Let your body speak to you as you dress, and though you can get great tips from blogs, Pinterest, or even friends on how to pull out shirtdress outfit – your instincts and motivation are what will make you noticed.

Printed T-Shirt with Thigh-High Boots

Show off your cool side by wearing an oversized printed T-shirt with the black thigh-high bootsPhoto: fromluxewithlove.com

Show off your cool side by wearing an oversized printed T-shirt with the black thigh-high boots. You can add denim jacket or style this combination with a cool military parka.

Black T-Shirt with Velvet Thigh-High Boots

That's why wearing over-the-knee boots is cool!Photo: dunelondon.com

Over-the-knee boots were causing big troubles to the girls. No everybody approved them – they are considered to be indecently and vulgar.

However, many fashion bloggers convinced us that wearing them is actually cool!

Sporty T-Shirt and Thigh-High Boots

A mix of sporty and elegant pieces can be quite challenging to wear, but it is also very stylish! This girl matches her everyday high boots with a basic oversized tee and a cap! The result is pretty amazing.Photo: meganbatoon.com

A mix of sporty and elegant pieces can be quite challenging to wear, but it is also very stylish!

This girl matches her everyday high boots with a basic oversized tee and a cap! The result is pretty amazing.

Shirtdress&Boots – Give It A Go

One is sure – high boots will be your new favorite footwear.

We see that they can be comfy, warm and most of all – they are very fashionable. Every stylish girl keeps them for fall and winter days.

So, what are you waiting for? Buy your high boots and style them with versatile shirtdresses.


Privacy Policy and Terms of Service